Neil was born in Prestatyn, North Wales, on 13 October 1942. His mother had been evacuated there during the blitz on Liverpool and his father was at sea with the Royal Navy. Neil and his mother returned to Liverpool in 1942 when the bombing had ceased and he attended West Derby School, where he passed his 11 plus exams. He next went to Liverpool Institute in Mount Street where he shared the same class as Paul McCartney for English and Art lessons.

George Harrison also attended the school but was in the class one year behind Paul and Neil. Neil was to comment, “My first encounter with George was behind the school’s air-raid shelters. This great mass of shaggy hair loomed up and an out-of-breath voice requested a quick drag of my Woodbine. It was one of the first cigarettes either of us had smoked. We spluttered our way through it bravely but gleefully. After that the three of us did lots of ridiculous things together. By the time we were ready to take the GCE exams we’d added John Lennon to our ‘Mad Lad’ gang. He was doing his first term at Liverpool College of Art which overlooks the Institute playground and we all got together in a students coffee bar at lunchtime.”

Neil took nine GCEs and gained eight, failing to pass on French. He left the Institute in July 1959 to study accountancy and remained with a local firm for two years, receiving a wage of fifty shillings (£2.50) per week as a trainee accountant. At the time he was living as a lodger in Pete Best’s house and it was through the Best connection that he became involved with the Beatles. Pete had joined the group and
traveled to Germany with them. On their return they were booked at the Casbah club and Mona Best asked Neil to make some posters announcing ‘The Return Of The Beatles.’

The group had relied on public transport to get them to local gigs, but by February 1961 it was obvious that they could no longer rely on that method of rushing from hall to hall. They’d tried a spell hiring Frank Garner to drive them to gigs, but he was the bouncer at the Casbah club and found he couldn’t keep the two jobs going at the same time.

Pete decided to approach Neil and ask him to drive them to their gigs. Pete suggested that he buy a van and commented, “He bought a battered old grey and maroon model for fifteen pounds (other sources say he bought a second-hand van for £80), but at least it went, which was the main consideration. So Neil entered enthusiastically the world of show business as our first roadie.” He charged each of them five shillings (25p)
per man, per gig.

By July 1962, on the group’s return from their second trip to Germany, Neil decided to take the plunge and become their official road manager, as he was now earning more money driving them around than as an accountant. He was also helping Mona Best, who he was living with, to run the Casbah club. The couple had a son Roag, but it has been suggested that they didn’t get married because it could have been detrimental to the health of her former husband, Johnny Best.